DE2311753C3 - Process for the preparation of aminobenzenes - Google Patents
Process for the preparation of aminobenzenesInfo
- Publication number
- DE2311753C3 DE2311753C3 DE19732311753 DE2311753A DE2311753C3 DE 2311753 C3 DE2311753 C3 DE 2311753C3 DE 19732311753 DE19732311753 DE 19732311753 DE 2311753 A DE2311753 A DE 2311753A DE 2311753 C3 DE2311753 C3 DE 2311753C3
- Authority
- DE
- Germany
- Prior art keywords
- acids
- molecular weight
- low molecular
- range
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001448 anilines Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000000875 corresponding Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WHNAMGUAXHGCHH-UHFFFAOYSA-N 1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1 WHNAMGUAXHGCHH-UHFFFAOYSA-N 0.000 description 4
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(Trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 229960002449 Glycine Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- NDZJSUCUYPZXPR-UHFFFAOYSA-N 1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C(F)(F)F NDZJSUCUYPZXPR-UHFFFAOYSA-N 0.000 description 2
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 229940021015 I.V. solution additive Amino Acids Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 229960003767 Alanine Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 229960005261 Aspartic Acid Drugs 0.000 description 1
- -1 Carboxylic acids aminocarboxylic acids Chemical class 0.000 description 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 1
- 229960002989 Glutamic Acid Drugs 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 229960003330 Pentetic Acid Drugs 0.000 description 1
- 229960005190 Phenylalanine Drugs 0.000 description 1
- 229940043230 Sarcosine Drugs 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 229960004799 Tryptophan Drugs 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N edta Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine zwitterion Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- ZAWGLAXBGYSUHN-UHFFFAOYSA-M sodium;2-[bis(carboxymethyl)amino]acetate Chemical compound [Na+].OC(=O)CN(CC(O)=O)CC([O-])=O ZAWGLAXBGYSUHN-UHFFFAOYSA-M 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Description
Gegenstand des Hauptpatents 22 40 849 ist ein Verfahren zur Herstellung von Aminobenzolen, die durch Halogen, aliphatische Sulfonyl- oder Halogenalkylgruppen substituiert sind, durch Hydrieren der entsprechenden Nitrobenzole in wäßriger Phase mit Hilfe von Nickel-Katalysatoren, das dadurch gekennzeichnet ist, daß man durch Zusatz von Sauerstoffsäuren des drei- oder fünfwertigen Phosphors, des Bors, der Kohlensäure oder niedermolekularer Carbonsäuren und ausreichend starken Basen bzw. entsprechender Salze einen pH-Bereich von 6 bis 7,5 einstellt und die Zusätze so dosiert, daß dieser Bereich im Laufe der Reaktion nicht unterschritten wird.The main patent 22 40 849 is a process for the preparation of aminobenzenes by Halogen, aliphatic sulfonyl or haloalkyl groups are substituted by hydrogenating the corresponding Nitrobenzenes in the aqueous phase with the help of nickel catalysts, which is characterized is that by adding oxo acids of trivalent or pentavalent phosphorus, boron, the Carbonic acid or low molecular weight carboxylic acids and sufficiently strong bases or equivalent Salts adjusts a pH range of 6 to 7.5 and doses the additives so that this range over the course of the Reaction is not undershot.
In weiterer Ausgestaltung dieses Erfindunpsgedankens wurde nun gefunden, daß besonders vorteilhafte Ergebnisse erzielt werden, wenn als niedermolekulare Carbonsäuren Aminocarbonsäuren eingesetzt werden.In a further embodiment of this inventive concept it has now been found that particularly advantageous results are achieved when as low molecular weight Carboxylic acids aminocarboxylic acids are used.
Unter niedermolekularen Aminocarbonsäuren sind - analog zum Hauptpatent - Aminoderivate von aliphatischen, araliphatischen oderaromatischen Mono- und Polycarbonsäuren mit bis zu etwa 10 Kohlenstoffatomen zu verstehen, wobei diese Säuren eine oder mehrere Amino- oder auch Imino- und Nitrilogruppen enthalten können. Es kommen natürliche Aminosäuren, wie Alanin, Valin, Leucin, Serin, Threonin, Arginin, Lysin, Asparaginsäure, Glutaminsäure, Phenylalanin oder Tryptophan, vor allem aber die technisch leicht zugänglichen Aminosäuren Sarkosin, /i-Alanin, i-Aminocapronsäure, insbesondere Glycin, Iminodiessigsäure, Nitrilotriessigsäure, Äthylendiamintetraessigsäure, Diäthylentriamin-pentaessigsäure oder N-//'-Hydroxyäthyl-äthylendiamin-triessigsäure in Betracht. Low molecular weight aminocarboxylic acids are - analogously to the main patent - amino derivatives of aliphatic, araliphatic or aromatic mono- and polycarboxylic acids with up to about 10 carbon atoms to understand, where these acids have one or more amino or imino and nitrile groups may contain. Natural amino acids such as alanine, valine, leucine, serine, threonine, Arginine, lysine, aspartic acid, glutamic acid, phenylalanine or tryptophan, but especially the technical ones easily accessible amino acids sarcosine, / i-alanine, i-aminocaproic acid, especially glycine, iminodiacetic acid, Nitrilotriacetic acid, ethylenediaminetetraacetic acid, diethylenetriamine-pentaacetic acid or N - // '- Hydroxyethyl-ethylenediamine-triacetic acid into consideration.
Die Basenkomponenten und Reaktionsbedingungen entsprechen denen des Hauptpatents.The base components and reaction conditions correspond to those of the main patent.
Es hat sich gezeigt, daß die erfindungsgemäßen Zusätze (»Promotoren«) eine hohe pH-stabilisierende Wirkung aufweisen und den Ablauf der Reaktion überaus günstig beeinflussen. Es ist deshalb insbesondere möglich, im oberen Bereich des in der Hauptanmeldung angegebenen Temperaturintervalls zu arbeiten, ohne daß hierbei in störendem Ausmaß Neben- und bzw. oder Folgereaktionen ablaufen. Die Anwendung höherer Temperaturen bringt dabei den Vorteil erheblich höherer Raum-Zeit-Ausbeuten mit sich.It has been shown that the additives according to the invention ("promoters") have a high pH-stabilizing effect Have an effect and influence the course of the reaction extremely favorably. It is therefore special possible to work in the upper range of the temperature range specified in the main application, without side and / or secondary reactions taking place to a disruptive extent. The application higher temperatures have the advantage of considerably higher space-time yields.
m-Nitrobenzotrifluorid wird in wäßriger Emulsion bei einem Wasserstoffdruck von ca. 40 atü und einer
Temperatur von 1000C in Gegenwart eines Nickel-Katalysators
unter Zusatz von Aminoessigsäure und wäßriger Natriumhydroxid-Lösung zu m-Aminobenzotrifluorid
hydriert. Die wäßrige Phase hat nach Reaktionsende einen pH-Wert von 7,0.
Nach der Hydrierung, Entspannung und Spülen des Druckreaktors mit Stickstoff wird der Reaktorinhalt
über ein Filteraggregat zur Isolierung des Kata'ysators
in einen Spitzkessel gedrückt, in welchem die Trennung der beiden Flüssigkeitsschichten vorgenommen
wird. Die organische Phase enthält das m-Aminobenzotrifluorid und hat im Vergleich zu der wäßrigen
Phase die höhere Dichte. Das rohe m-Aminobenzotrilluorid
weist nach Trocknung einen Gehalt an m-Toluidin von weniger als 0,1 Gew.-% auf.
Mengeneinsatz:m-nitrobenzotrifluoride is atmospheres and in aqueous emulsion at a hydrogen pressure of approximately 40 a temperature of 100 0 C in the presence of a nickel catalyst with addition of aminoacetic acid and aqueous sodium hydroxide solution to m-aminobenzotrifluoride hydrogenated. After the end of the reaction, the aqueous phase has a pH of 7.0.
After the hydrogenation, depressurization and purging of the pressure reactor with nitrogen, the reactor contents are pressed through a filter unit to isolate the catalyst into a pointed kettle in which the two layers of liquid are separated. The organic phase contains the m-aminobenzotrifluoride and has a higher density compared to the aqueous phase. The crude m-aminobenzotrilluoride has, after drying, an m-toluidine content of less than 0.1% by weight.
Quantity stake:
1150 g m-Nitrobenzotrifluorid
480 NL Wasserstoff (einschließlich Spülwasserstoff) 1150 g of m-nitrobenzotrifluoride
480 NL hydrogen (including flushing hydrogen)
22 g 33%ige wäßrige Natriumhydroxidlösung 17 g Aminoessigsäure
11,5 g Nickel-Katalysator
600 ml Wasser
Ausbeute an Rohprodukt: 98% der Theorie.22 g of 33% strength aqueous sodium hydroxide solution, 17 g of aminoacetic acid
11.5 grams of nickel catalyst
600 ml of water
Yield of crude product: 98% of theory.
m-Nitrobenzotrifluorid wird - mit Wasser vermischt - bei einem Wasserstoffdruck von ca. 40 atü und einer
Temperatur von 800C in Gegenwart eines Nickelkatalysators
unter Zusatz des Trinatriumsalzes der Nitrilotriessigsäure zu m-Aminobenzotrifluorid hydriert.
Die wäßrige Phase hat am Ende der Hydrierung einen pH-Wert von 7,9. Die Durchführung der Hydrierung
und Aufarbeitung des Reaktionsgemisches erfolgen in der gleichen Weise wie in Beispiel 1 angegeben.
Das rohe, getrocknete m-Aminobenzotrifluorid enthält weniger als 0,1 % m-Toluidin.m-nitrobenzotrifluoride is - mixed with water - hydrogenated to m-aminobenzotrifluoride at a hydrogen pressure of about 40 atmospheres and a temperature of 80 ° C. in the presence of a nickel catalyst with the addition of the trisodium salt of nitrilotriacetic acid.
The aqueous phase has a pH of 7.9 at the end of the hydrogenation. The hydrogenation and work-up of the reaction mixture are carried out in the same way as indicated in Example 1. The crude, dried m-aminobenzotrifluoride contains less than 0.1% m-toluidine.
Mengeneinsatz:Quantity stake:
1150 g m-Nitrobenzotrifluorid
480 NL Wasserstoff (einschließlich Spülwasserstoff)
8,5 g Natrium-nitrilotriacetat1150 g of m-nitrobenzotrifluoride
480 NL hydrogen (including flushing hydrogen)
8.5 g sodium nitrilotriacetate
11 g Nickel-Katalysator
600 ml Wasser11 g nickel catalyst
600 ml of water
Ausbeute an Rohprodukt: 98% der Theorie.
Beispiel 3Yield of crude product: 98% of theory.
Example 3
o-Nitrobenzotrifluorid wird in wäßriger Emulsion bei einem Wasserstoffdruck von ca. 40 atü und einer Temperatur von 900C in Gegenwart eines Nickelkatalysator unter Zusatz des Tetranatriumsalzes der Äthylendiaminotetraessigsäure zu o-Aminobenzotrifluorid hydriert. Der End-pH-Wert der wäßrigen Phase des Reaktionssystems beträgt 7,0.o-nitrobenzotrifluoride is hydrogenated to o-aminobenzotrifluoride atm and in aqueous emulsion at a hydrogen pressure of about 40 at a temperature of 90 0 C in the presence of a nickel catalyst, with the addition of tetrasodium salt of ethylenediaminotetraacetic acid. The final pH of the aqueous phase of the reaction system is 7.0.
Die Durchführung der katalytischen Hydrierung und Aufarbeitung des Reaktionsgemisches erfoigen in gleicher Weise wie in Beispiel 1 aufgeführt. Das rohe, getrocknete, o-Aminobenzotrifluorid enthält weniger als0,l%o-Toluidin.The catalytic hydrogenation and work-up of the reaction mixture are carried out in in the same way as in Example 1. The raw, dried, o-aminobenzotrifluoride contains less as 0.1% o-toluidine.
Mcngcncinsat/:Mcngcncinsat /:
115Og o-Nitrobenzotrifluorid 480 NU Wasserstoff (einschließlich Spükvasser-115Og o-nitrobenzotrifluoride 480 NU hydrogen (including flushing water
sto ff)material)
8,5 g Tetranalrium-älhylendiaminotetra-acctiit
Il g Nickel-Katalysator
600 ml Wasser8.5 g of tetra-aluminum-ethylenediamine-tetra-activity II g of nickel catalyst
600 ml of water
Ausbeute an Rohprodukt: ')8% der Theorie.Yield of crude product: ') 8% of theory.
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732311753 DE2311753C3 (en) | 1973-03-09 | Process for the preparation of aminobenzenes | |
| NL7311193A NL7311193A (en) | 1972-08-19 | 1973-08-14 | |
| IL43009A IL43009A (en) | 1972-08-19 | 1973-08-16 | Process for preparing aminobenzenes |
| FR7329968A FR2196321B1 (en) | 1972-08-19 | 1973-08-17 | |
| CA179,033A CA994359A (en) | 1972-08-19 | 1973-08-17 | Process for preparing aminobenzenes |
| SE7311223A SE402762B (en) | 1972-08-19 | 1973-08-17 | PROCEDURE FOR THE PREPARATION OF AMINOBENSENES WHICH ARE SUBSTITUTED WITH HALOGENIC ALIFATIC SULPHONYL OR HALOGENALKYL GROUPS FROM THE CORRESPONDING NITROBENSENES |
| JP9181373A JPS5620306B2 (en) | 1972-08-19 | 1973-08-17 | |
| IT27971/73A IT1001529B (en) | 1972-08-19 | 1973-08-17 | PROCEDURE FOR THE PREPARATION OF AMINOBENZENES |
| GB3931973A GB1440991A (en) | 1972-08-19 | 1973-08-20 | Process for preparaing aminobenzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732311753 DE2311753C3 (en) | 1973-03-09 | Process for the preparation of aminobenzenes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2311753A1 DE2311753A1 (en) | 1974-09-12 |
| DE2311753B2 DE2311753B2 (en) | 1977-04-07 |
| DE2311753C3 true DE2311753C3 (en) | 1977-12-01 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60124482T2 (en) | Process for the preparation of xylylenediamine | |
| DE1930267A1 (en) | Removal of trans-2-pentenenitrile from 3- and 4-pentenenitrile | |
| DE69629136T2 (en) | Process for the preparation of ruthenium hydrogenation catalysts and their use | |
| DE2807816C2 (en) | ||
| DE2336852A1 (en) | PROCESS FOR MANUFACTURING ORGANIC NITRILES | |
| DE69624519T2 (en) | Ruthenium complex-containing catalyst, its use in the hydrogenation of unsaturated substrates, especially organic nitriles | |
| DE3131047A1 (en) | METHOD FOR ISOMERIZING 2-METHYL-3-BUTENNITRILE | |
| DE1002342C2 (en) | Process for the preparation of ª ‡ -monocyanaethylated ketones | |
| DE2009470A1 (en) | Process for the production of unsaturated nitriles | |
| DE2311753C3 (en) | Process for the preparation of aminobenzenes | |
| CH374979A (en) | Process for the production of aromatic carboxylic acids | |
| DE2311753B2 (en) | PROCESS FOR THE PRODUCTION OF AMINOBENZENE | |
| DE2301411C3 (en) | Process for the preparation of Aminoäthylphosphonaten | |
| DE60209623T2 (en) | Process for the preparation of a nitrile compound | |
| DE2609209C2 (en) | Process for the preparation of 2-pyrrolidone | |
| DE743967C (en) | Process for the preparation of dinitriles | |
| EP0065294A1 (en) | Process for preparing formylcyanonorbornane | |
| CH623804A5 (en) | ||
| DE2217494C2 (en) | Process for the preparation of alkoxypropionitriles | |
| CH270546A (en) | Method for producing a polyamide. | |
| EP1511720A1 (en) | Method for reducing the content of an unsaturated amine in a mixture containing an amino nitrile, a diamine, a dinitrile or mixtures thereof | |
| DD253947A1 (en) | METHOD FOR PRODUCING CHIRAL TRANSITION METAL COMPLEX CATALYSTS | |
| CH378868A (en) | Process for the preparation of w-amino-caprylic acid amide | |
| DE3009604A1 (en) | METHOD FOR PRODUCING BUTYROLACTONES | |
| AT229025B (en) | Process for the preparation of catalysts for the polymerization of olefins |